Sunday, February 17, 2013

Lordy, Lordy, Look Who's Forty!

sissy gets fucked like a girl

When we arrived in our room the first thing I did was order tia to strip and kneel so I could fasten the leather training collar (the very same one I led him in to Petsmart to choose four years ago) around his neck.

Then the next thing I did was make him put his clothes BACK on so he could go out and fetch the ice I forgot! :p

After he'd returned, and executed the prime directive of making me a drink (with plenty of ice), I ordered him to strip once more. The chastity device went on next and then my clothes came off. I was eager to try out that jacuzzi tub! I soaked in the tub while the birthday slut prepared his anal fuckhole with multiple enemas. Accompanied by much mockery and amusement from me of course. At last I stepped out of the tub and my freshly-cleansed slave was allowed to dry me off, Princess Ardala style.

We adjourned to the next room, where there was more light, and I had my sissy kneel at my feet so I could do her makeup. While we were thus engaged our friends Mistress Candice and her girl emma knocked on the door. They'd just arrived, having driven down from Jacksonville for the occasion, and I invited them in for a quick chat despite tia's embarrassed nakedness.

After catching up a bit the ladies left to go freshen up themselves, and I recommenced with my pretty pet's feminine transformation. I dressed her in a stretchy pink fishnet top that left her nipples exposed for me to play with, tiny grey thong panties trimmed with rainbow details that framed her ass so sweetly, and finally pale pink thigh-high socks to set off her sexy, curvy legs. The finishing touch was her wig of soft blonde curls and voila, my sexy shemale lover knelt trembling before me.

I'd been fielding text messages & emails from various people throughout the afternoon; many of our prospective guests sent their regrets at the last minute. But two solo crossdressing girls, Stephanie and Aida, were still coming. Stephanie showed up shortly after I'd got tia dressed and while the birthday slave fixed drinks for everyone she and I commenced the first round of 'Truth or Dare'. Within the first few minutes of the game my smart-assed slut had managed to earn two penalties: the first administered in the form of a swift blow to the right buttock with a large wooden spoon, and the second being the forceful insertion of a small dildo (the one we call 'fairy') into her tight ass.

Soon all the guests were assembled, my good little sissy had fetched drinks for everybody, and we were laughing through more rounds of 'Truth or Dare'. One girl's skirt was raised to give us all a good look at her CB-3000 chastity device...another was ordered to crawl around and kiss everyone's feet...a number of titillating confessions were made...and eventually tia wound up on my lap, demonstrating her stripper moves. Which was made that much more interesting by my simultaneously trying on a new thigh-harness loaded with her favorite dildo, which shall henceforth be called Prince Charming. She put on a good show, at least from my perspective, and pictures were taken.

The rounds of the game continued and somewhere along the way emma lost her clothes. (And tia lost her chastity cage.) We all watched as emma's Mistress led her over, naked and crawling on a leash, to render some oral service to a very excited Stephanie. I pulled out my cellphone and snapped some pics at Candice & Stephanie's request but I was soon distracted by groping and molesting my own sexy slavegirl.

Alas Stephanie had to leave early, so I announced it was time for the birthday spankings. Since she had to go soon Stephanie went first, administering eight sensual bare-handed smacks to my pet's thong-framed bottom. Well, I say eight - it was actually more due to my foolish slave having forgotten to keep count. Stephanie also went second, lying across my lap herself and taking a matching set of eight smacks on her own bare bottom from me. Emma declined to be a swatter and so her share of eight blows was split between myself and Mistress Candice, who went next.

Ms. Candice is an old school ass-kicking kind of domme, well known for the intensity of her pain play, so I knew the next dozen blows would be rough on my fragile darling. Therefore I decided to sweeten the experience - and muffle the noise! - by wrapping my strong curvy legs around tia's head, pressing her shrieking mouth into my crotch and smothering her between my soft thighs. I'm not sure whether it helped my little sissy to bear the pain of having Ms Candice wield the hated red leather slapper on her ass, but I certainly enjoyed the experience of having her crying into my pantied crotch.

At last it was MY turn. Aida had ceded her share of the spankings to me so I now had 20 swats to deliver. I'd opted to use the relatively tame black leather paddle with the fluffy sheepskin on one side but I decided to liven things up by inserting Prince Charming into tia's rectum before I started. (The smaller fairy dildo, which I'd stuck in her earlier as a smart-ass penalty, had been removed after about 20 minutes.) I then proceeded to dole out my 20 swats, taking care to aim the paddle to precisely hit the end of the dildo sticking out of her ass. I even got in a few swats with the handle of the paddle, turned so as to strike down on her dangling testicles as it pushed the dildo sharply into her. All in all she was not so much being spanked as being raped with the paddle. *evilgrin*

For the most part during this paddling I knelt beside her on the bed. But at one point I had tia pinned down, with my leg draped across her back and shoulders and my foot pressing her face into the bed. Sadly my damned hip wouldn't let me hold that position for long, and by the time I'd finished administering tia's 40th birthday spanking I was ready to give that injured joint a rest. I might normally, at this point, leave her kneeling on the bed and bugger her from behind. Instead I laid down on my back and ordered her to climb on top of me and ride me cowgirl style.

Being made to perform like the sluttiest porn whore, ride a cock and cum from it in front of a room full of observers, might not have been on tia's bucket list. But making her do it has certainly been on mine! It was so hot to have my beautiful shemale fucktoy moving on top of me, writhing and moaning as I groped her body and murmured nasty things to her. I reminded her that she'd need to be able to do this for her boyfriend someday, and for any other men I decided to give her to. She'd need to be able to bounce and grind on their dicks, doing all the work for them and convincing them that she was desperate to have every inch inside her. Convincing them that she was as horny as a bitch in heat and wanted nothing more than to have her fuckholes stuffed any way they wanted to give it to her. Which shouldn't be hard considering that she really was a horny little slut desperate to get fucked, I mean, look at how she was performing right now in front of her birthday party guests...

I kept it up for a little while, I'm not sure how long, before I ordered her to cum for me. She exploded with shuddering groans that turned to whimpers as I reached down into her panties and peeled off the condom which had captured her spurting cream. She grimaced, but obediently opened her mouth and sucked down every drop.

The party broke up not long afterward and I think we were both quite happy to fall into bed. But the next morning I could not stop thinking of how beautiful she'd looked moving on top of me...and how much I wanted to have her like that again. Something about not just forcing her to submit to getting fucked but forcing her to actually DO the fucking was incredibly hot. It shows how much of a slave she's become, how much her training has taken hold, that she not only CAN do these things and WILL do them, but that she literally gets off on doing them. I remember the days when my putting anything in her ass was an instant erection killer...now here she is begging to be buggered all the time!

So early on, before either of us was dressed or had eaten or anything, I put Prince Charming in my usual harness and slipped it on. I laid back in the bed and once again ordered her to climb on top of me. I made her rub against it, comparing her dainty cockette to its length and girth. Then I made her squirt a glob of lube on the end and rub my plastic phallus up and down the crack of her ass. I pulled her head down to kiss her and growl a few more lewd comments about the previous night in her ear. By now she was whimpering and squirming, and that cockette was throbbingly hard between our bodies. I knew she wanted me inside her, knew she wanted to be fucked again...and I laughed as I pushed her off me and ordered her to put her boy clothes on and go procure some breakfast.

By the time she came back I was dozing off again and I wanted to stay asleep for a while. So I told her to go have a shower, fetch more ice and pack up our things while I slept. About an hour and a half later I woke again and as I stretched and yawned my attentive pet offered me a fresh drink and some fruit she'd brought me from the hotel buffet. I ate a banana then got up and rummaged around in our bags for a couple minutes. Tossing some sheer ruffled panties, a pair of breastforms, and a pink satin bra at her, I ordered "put these on bitch". I think she must have gotten instantly hard; certainly that little cockette was sticking straight out again as soon as she pulled her panties up over it. The blonde wig came next (no time for makeup alas) followed by the leather training collar she'd taken off before showering, and a fresh condom. Just a matter of moments and there was my horny shemale sex slave standing before me once more.

I loaded Prince Charming back into the thigh harness and climbed back into bed. Once again I ordered her to get on top of me; this time I spent only a few moments groping her before I ordered her to reach around and guide my cock into her hungry fuckhole. I felt her muscles twitching around the dildo, the movement transmitted to my skin by the silicone shaft, and she moaned as it sank deeper into her. When my strapon was firmly implanted in her twitching anus she began to hump against my leg. I stilled her movements and adjusted our positions so that she was straddling my left thigh (the one with the harness) and her own left thigh was held between my legs. As she resumed humping back against me I reached down between my own legs and started rubbing my clit. I talked to her, telling her how beautifully slutty she was and describing the ways in which I and others might want to make use of that slutty body in the future. She was soon whimpering and shaking, her eyes rolled back in her head and wearing that unmistakeable look of being a hair's breadth from orgasm. "Do you want to cum slut? Beg me for it!" I purred and without hesitation a torrent of words tumbled out "please Mistress please your horny sissy slut wants to cum so bad please Mistress I'll do anything please.." I laughed "of course you will slave. And now you're going to cum for me. Cum from being fucked like a girl, cum like you did in front of all our guests last night." And cum she did, blushing bright red while she once more filled a condom full of her sissy cream.

I gave her a little shove and she collapsed on the bed beside me, the dildo sliding out of her ass with a tiny, wet plop. I unfastened it from my thigh and dropped it to the floor, then reached for one more toy - the ever faithful gizmo. Sliding the cum-filled condom off her wilting cockette, I drizzled its contents all over the gag side of our gag-mounted dildo toy and pushed it into her mouth. She grimaced at the taste but obediently lowered her head, allowing me to buckle it firmly in place. The, grabbing the dildo which now stuck straight out from her face, I guided her down between my things and into my sopping wet pussy.

I'd had a very small orgasm the night before when she was riding me; I was more than ready for a proper release of my own. And when it came it was magnificent, explosive waves of pleasure crashing through my body and washing away (for the moment anyhow) all the pain of my injured hip. It felt so good I almost cried afterward. Funny how something so simple can instantly make life brighter & sweeter. No matter how bad I might be hurting I could still wallow in the hedonistic pleasures of the flesh with my beautiful birthday girl. :)


I've mentioned a couple of times in this account that I'm not in top form. Shortly before xmas I did something to my hip which has kept me in more or less constant pain ever since. In retrospect I probably shouldn't have even tried to host a party in my condition; I suppose I thought it would surely be healed up by the time February rolled around. Anyway, the end result was that this party was a lot tamer than I'd meant it to be. Now, writing this, I can see that the x-rated action which did take place would have been wildest-fantasy material for a lot of sissies. Which I guess says something about what a lucky sissy slut tia really is. ;)

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